Home

Citation: WANG Li, ZHU Cui-Hong, ZHANG Xiang-Wen, MI Zhen-Tao. Synthesis of 3β-Hydroxy-16α,17α,21-trimethyl-5-en-20-one[J]. Chinese Journal of Applied Chemistry, ;2002, 19(12): 1189-1191. shu

Synthesis of 3β-Hydroxy-16α,17α,21-trimethyl-5-en-20-one

1.
a School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072;
2.
b Tianjin Pharmaceuticals Corp. Ltd., Tianjin

Corresponding author: WANG Li,
Received Date: 29 May 2002
Available Online: 3 September 2002
Fund Project: 天津药业有限公司博士后科研基金资助(199902) (199902)

3U-Hydroxy-16T,17T,21-trimethyl-5-en-20-one was synthesized from 3T-acetoxypregna-5,16-dien-20-one and characterized by elemental analysis, ¹H NMR, MS and IR. 16T,17T-Dimethyl steroid was formed by treatment of 3U-acetoxypregna-5,16-dien-20-one with methylmagnesium bromide, followed by reaction of the resulting 17(20)-enolate with methyl iodide. The main by-products were 3U-hydroxy-16T,17T-dimethyl-5-en-20-one. LHDMS([(CH₃)₃Si]₂NLi) and LDA([(CH₃)₂CH]₂NLi) were chosen as proper reagents for 21-position alkylation. The almost quantitative conversion of 16T,17T-dimethyl corticosteroid was achieved and the highest yield of the 16T,17T,21-trimethyl corticosteroid was 78%. The optimum reaction temperature was -20℃ for 16T,17T-dialkylation and was -50℃ for 21-position alkylation.
- corticosteroid,
- alkylation,
- conjugate addition,
- Rimexolone
1. [1]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
2. [2]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
3. [3]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
4. [4]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
5. [5]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
6. [6]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
7. [7]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
8. [8]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
9. [9]
  Ruolin CHENG , Yue WANG , Xiyao NIU , Huagen LIANG , Ling LIU , Shijian LU . Efficient photothermal catalytic CO₂ cycloaddition over W₁₈O₄₉/rGO composites. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1276-1284. doi: 10.11862/CJIC.20240424
10. [10]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
11. [11]
  Minghui Wu , Markus Mühlinghaus , Xuechao Li , Chaojie Xu , Qiang Chen , Haiming Zhang , Klaus Müllen , Lifeng Chi . On-Surface Synthesis of Chevron-Shaped Conjugated Ladder Polymers Consisting of Benzo[a]azulene Units. Acta Physico-Chimica Sinica, 2024, 40(8): 2307024-0. doi: 10.3866/PKU.WHXB202307024
12. [12]
  Yan Xiao , Shuling Li , Yifan Li , Jianing Fan , Linlin Shi . Discovering the Beauty of Life: Adding Some “Ingredients” to Crystals. University Chemistry, 2024, 39(6): 366-372. doi: 10.3866/PKU.DXHX202312025
13. [13]
  Yuheng Zhou . 大学课堂的色彩——探索过渡元素的美. University Chemistry, 2025, 40(6): 303-309. doi: 10.12461/PKU.DXHX202407110
14. [14]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
15. [15]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
16. [16]
  Xudong Liu , Huili Fan , Junping Xiao , Min Yang , Yan Li . Teaching Approaches to the A_E + A_N Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041
17. [17]
  Zishuo Yi , Peng Liu , Yan Xu . Fluorescent “Chameleon”: A Popular Science Experiment Based on Dynamic Luminescence. University Chemistry, 2024, 39(9): 304-310. doi: 10.12461/PKU.DXHX202311079
18. [18]
  Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049
19. [19]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . Optimizing interfacial electric fields in carbon nitride nanosheet/spherical conjugated polymer S-scheme heterojunction for hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-0. doi: 10.1016/j.actphy.2025.100095
20. [20]
  Ruonan Li , Shijie Liang , Yunhua Xu , Cuifen Zhang , Zheng Tang , Baiqiao Liu , Weiwei Li . Chlorine-Substituted Double-Cable Conjugated Polymers with Near-Infrared Absorption for Low Energy Loss Single-Component Organic Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(8): 2307037-0. doi: 10.3866/PKU.WHXB202307037

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(350)
HTML views(47)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return